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N,N,N',N'-quaterphenyl polycarboxylic aryl diamine synthesizing method

A technology for tetrabiphenyl polyacid aryl diamine and tetrabiphenyl polycarboxylic acid aryl diamine compound, which is applied in the field of organic synthesis, can solve the problems of complicated preparation, many reaction steps and the like, and achieves economical and efficient reaction and simple operation. , cheap and wide range of effects

Inactive Publication Date: 2017-05-24
LUOYANG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

For example: the synthesis of N, N, N´, N´-tetraphenylpolycarboxylic acid aryldiamine, but these synthesis methods have more reaction steps and their preparation is more cumbersome, which makes them subject to certain restrictions in application

Method used

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  • N,N,N',N'-quaterphenyl polycarboxylic aryl diamine synthesizing method
  • N,N,N',N'-quaterphenyl polycarboxylic aryl diamine synthesizing method
  • N,N,N',N'-quaterphenyl polycarboxylic aryl diamine synthesizing method

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Embodiment 1

[0019] N, N, N´, N´-quaterphenyl polycarboxylic acid aryl diamine compounds, the specific structure can be:

[0020]

[0021]

[0022]

Embodiment 2

[0024] Preparation of N, N, N´, N´-quaterphenyl polycarboxylic acid aryldiamine compound (1): under nitrogen protection, transfer to a 10 ml Schlek reaction tube (one commonly used in anhydrous and oxygen-free operation) glass instrument) by adding 1.0mmol 4,4´-diiodobiphenyl, 2.0mmol bis(4-bromophenyl)amine, 0.05mmol palladium acetate, 0.05mmol dicyclohexyl (3,6-dimethoxy-2 ',4',6'-triisopropyl(1,1'-biphenyl)-2-yl)phosphine, 3.0mmol sodium tert-butoxide, and 5ml toluene, replace the reaction tube with nitrogen three times, and then Heated to 90°C with an oil bath while stirring, and the reaction was refluxed for 24 hours. Lowered to room temperature; then to the reaction solution, 4.0mmol 4-carboxyphenylboronic acid, 0.05mmol palladium acetate, 0.05mmol 2'-dicyclohexyl-2,6-dimethoxy-3-sulfonic acid-1,1'- Biphenyl sodium salt, 8.0 mmol potassium carbonate, and 100 mmol water; then heated to 100° C. in an oil bath under magnetic stirring, and the reaction was refluxed for 24 h...

Embodiment 3

[0026] Preparation of N, N, N´, N´-quaterphenyl polycarboxylic acid aryldiamine compound (3): under nitrogen protection, transfer to a 10 ml Schlek reaction tube (a commonly used one for anhydrous and anaerobic operation) glass instrument) by adding 1.0mmol 4,4´-dibromobiphenyl, 3.0mmol bis(4-bromophenyl)amine, 0.10mmol palladium chloride, 0.10mmol di-tert-butyl (2',4',6' -triisopropyl-3,6-dimethoxybiphenyl-2-yl)phosphine, 6.0mmol potassium tert-butoxide, and 5ml dioxane, replace the reaction tube with nitrogen for 3 times, and then Under heating with an oil bath to 110°C, the reaction was refluxed for 48 hours. Lowered to room temperature; then to the reaction solution, 8.0mmol 3,5-dicarboxyphenylboronic acid, 0.10mmol palladium acetate, 0.10mmol 2'-dicyclohexylphosphino-2,6-di-I-propyl-4-sulfonate Acetate-1,1'-sodium biphenyl, 16.0 mmol cesium carbonate, and 200 mmol water; then heated to 110° C. in an oil bath under magnetic stirring, and the reaction was refluxed for 48 h...

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Abstract

The invention relates to an N,N,N',N'-quaterphenyl polycarboxylic aryl diamine compound synthesizing method. According to the synthesizing method, a palladium catalyst one-pot method is utilized to catalyze carbon-nitrogen coupled reaction of dual-halogen aromatic hydrocarbon and bis(4-halogenphenyl)amine and carbon-carbon coupled reaction of carboxyl phenylboronic acid, and an obtained product is acidized to obtain N,N,N',N'-quaterphenyl polycarboxylic aryl diamine compound. A preparation method of the compound comprises the steps of taking bis(4-halogenphenyl)amine, dual-halogen aromatic hydrocarbon, palladium chloride, phosphorus ligand and alkali, adding into an organic solvent, heating in N2 gas protection and cooling to room temperature after reaction finishes; then adding carboxyl phenylboronic acid, palladium chloride, phosphorus ligand, alkali and water, filtering after reaction finishes and acidizing obtained solid to obtain the N,N,N',N'-quaterphenyl polycarboxylic aryl diamine compound. The used palladium catalyst is easy to obtain, short in reaction route, cheap in substances, wide in range and favorable for industrial production.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a synthesis method of N,N,N',N'-quaterphenyl polyacid aryl diamine. Background technique [0002] Aromatic carboxylic acids are important intermediates in the synthesis of drugs, pesticides, liquid crystals, etc., and their application fields continue to expand, and they are valued by people. For example: Pentafluorobenzoic acid can be used in the synthesis of pyrethrins and liquid crystals. In addition, aromatic carboxylic acids play an important role as ligands in coordination polymers and assembled supramolecules. Among them, aromatic polycarboxylic acid has rigid structure, multi-coordination sites, diversified coordination modes and rich weak interactions between solvent molecules. These properties are beneficial for people to design molecules with specific shapes and structures, and to construct functional complexes with various configurations. Aromatic carboxy...

Claims

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Application Information

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IPC IPC(8): C07D471/04C07D213/74C07D221/10C07C227/08C07C229/52C07C209/10C07C211/56C07C211/59C07C211/61
CPCC07C209/10C07C227/08C07D213/74C07D221/10C07D471/04C07C229/52C07C211/56C07C211/59C07C211/61
Inventor 徐晨薛东旭李红梅王志强付维军
Owner LUOYANG NORMAL UNIV